In October 2016, Vanity Fair made a video of four of its cartoonists—Edward Sorel, Steve Brodner, Philip Burke, and Robert Risko—drawing Donald Trump. They were clearly enjoying themselves, exploring every aspect of his physique: his “girth,” the fact that “there’s so much of him” (Burke); the hair that is “essentially a beret that is flipped forward on his head” (Risko); the eyes that show “greed, disdain” (Burke); the “marvelously ratlike” nose (Brodner); the mouth that is a “sphincter muscle” (Risko); the “sleazy” look (Sorel); the facial features that resemble “piss holes in the snow” (Brodner).

And now? How have artists and cartoonists been dealing with Trump since he became president? We’ve seen cartoons of the orange potus smooching Vladimir Putin and groping the Statue of Liberty. We’ve seen him drawn (by Barry Blitt in The New Yorker) as a fat-assed golfer driving balls into the White House. We’ve seen him caricatured (by Pat Oliphant for The Nib) as a preening SS officer being heiled by Steve Bannon. We’ve seen him portrayed (by Signe Wilkinson of the Philadelphia Daily News) linking arms with a Confederate and a Nazi. We’ve seen him depicted (by Mike Luckovich of The Atlanta Journal-Constitution) as Jabba the Hutt, holding Lady Liberty in chains. We’ve seen him represented (by Matt Wuerker in Politico) as a kook in a straitjacket. We’ve seen him rendered (by Ann Telnaes of The Washington Post) as a red-faced fathead sitting on the toilet while he plots to pull out of the Paris climate accord.

But has any cartoon or drawing really riled Trump’s camp or given comfort to his foes the way Stephen Colbert’s regular pummeling on late-night television and Alec Baldwin’s impressions on Saturday Night Live do? Has any image proved indelible? I can’t think of any. Why is cartooning so tricky in the age of Trump?

Not long after Trump was elected, I went to the Hauser & Wirth gallery in New York, to an exhibition of Philip Guston’s drawings of Richard M. Nixon, all from the early 1970s. I’d seen them before, but this time the work—featuring Nixon as a walking nose, Secretary of State Henry Kissinger as a pair of black horn-rimmed glasses, and Vice President Spiro Agnew as a triangle studded with nails—had new resonance. In one of the drawings, Nixon was a Ku Klux Klansman conferring with his hooded colleagues (you could still tell who was who). In another, Nixon’s nose doubled as a phallus (a Tricky Dick, get it?) and testicles (with a 5 o’clock shadow) in bed with a bunch of other dicks.

These drawings were funny, mean, satisfying, and yet strangely soulful, too. Somehow they seemed to get at the tragic connection between the body of Nixon and his very essence—sneaky, paranoid, morally impoverished, lonely, resentful. Walking through that exhibition, I felt a wave of catharsis, nostalgia, and envy. How I wished Guston were alive to draw Trump!

Some people say we are in a Nixon moment. Talk of impeachment is in the air. Outrage against the current president has reached a pitch not seen since Watergate days. Yet can you think of a drawing of Trump that comes anywhere near Guston’s Nixon? Why not? Let me float some ideas by you in the form of 20 questions.

NO. 1: IS ANYONE OUT THERE MOTIVATED ENOUGH?

When Philip Guston put down his paintbrush and picked up his pen against Nixon, he explained his motivation: “The war, what was happening to America, the brutality of the world. What kind of man am I, sitting at home, reading magazines, going into frustrated fury about everything—and then going into my studio to adjust a red to a blue?”

His example makes you wonder: Are artists today moved enough to stop whatever they’re doing to work on Trump? They say they are. Take Pranas T. Naujokaitis, the illustrator of the children’s book Belches, Burps, and Farts: Oh My! In September, at the Small Press Expo for cartoons and graphic novels, in Bethesda, Maryland, he said that after Trump’s election, “it seemed trivial to be doing the usual thing.” Shannon Wheeler, the cartoonist behind the character Too Much Coffee Man, agreed. He started drawing Too Much Covfefe Man and illustrating the president’s tweets.

NO. 2: HOW CAN YOU BLAME A CHILD?

Motivated though they may be, many cartoonists have chosen a likeness for Trump that is disarming. Trump is often lampooned as a baby or toddler with no impulse control—sitting on the potty tweeting, throwing around food from his high chair, being mollified with little rockets. The Trump in Wheeler’s Sh*t My President Says: The Illustrated Tweets of Donald J. Trump looks like a self-satisfied Charlie Brown. In Trump’s ABC, Ann Telnaes portrays Trump as a plump, ill-tempered, red-faced infant. In The Unquotable Trump, R. Sikoryak includes a parody of Little Lulu, titled “Little Flunky,” in which Trump appears as a brat who throws a fit when he doesn’t get to be first at bat. (“Our system is absolutely, totally rigged!”) They’re all kind of funny, and apt. But what is the subtext? That Trump, the petulant child, can’t be held responsible for the damage he does?

Ann Telnaes (Trump’s ABC, Fantagraphics)

NO. 3: WHO WANTS TO GET THAT CLOSE?

I suspect that some cartoonists draw Trump as a child because they are repelled by his adult body. Caricaturing someone is like preparing to mimic him; it helps to look in the mirror and try to inhabit that person, which means getting pretty familiar with his head, body, gestures, and, in Trump’s case, toilet habits and sex practices. Here revulsion can creep in. Plus there may be limits regarding which of Trump’s body parts one can, in good conscience, shame. As Sikoryak says, it might be okay to call him a “short-fingered vulgarian,” as Spy magazine famously did decades ago (which, by the way, really got under Trump’s skin). But what about those nude statues of Trump with a micro-penis and no testicles (commissioned by the anarchist collective Indecline) briefly unveiled in Cleveland, Los Angeles, New York City, San Francisco, and Seattle in 2016? Don’t they amount to body shaming the president?

NO. 4: WHEN THEY GO LOW, SHOULDN’T WE GO HIGH?

Figuring out what the rules of satire should be in the Trump era is hard because we are currently under the administration of the body shamer in chief. Let’s look at the archive: Trump has attempted to shame Megyn Kelly, then of Fox News (“blood coming out of her wherever”), MSNBC’s Mika Brzezinski (“bleeding badly from a face-lift”), the teenage Latina winner of the Miss Universe beauty contest Alicia Machado (the “incredible bulk”), Rosie O’Donnell (“slob”), and The New York Times’s Serge Kovaleski (by mocking his disability). You might think it would be delicious justice to body shame this man in a caricature. But, oddly, many newspaper cartoonists have avoided doing so. Maybe they have internalized the rallying cry Michelle Obama issued during her memorable speech in support of Hillary Clinton at the 2016 Democratic National Convention: “When they go low, we go high.”

NO. 5: CAN CARTOONISTS AVOID BECOMING COLLABORATORS?

In looking for the right level of humor, satirists have found one reliable and renewable source of comedy—Trump’s tweets, which are emitted almost daily. Many Trump comic books published so far—including Warren Craghead III’s TrumpTrump, Sikoryak’s The Unquotable Trump, and Wheeler’s Sh*t My President Says—are partly tweet-based. While the mimicry is meant to mock, it brings its own set of worries: Putting Trump’s words and tweets into comics form gives the man more airtime and makes him seem like a comedian. He’s essentially writing his own material, and so cartoonists effectively become his creative collaborators. As Wheeler notes, “Trump is the writer and I am the artist.”

NO. 6: ISN’T TRUMP GETTING ENOUGH ATTENTION?

So how do you lampoon Trump without working for him? The cartoonist Keith Knight noted at the Small Press Expo that some cartoonists realize Trump’s personality is stealing “attention away from the issues”—racism, police brutality, poverty, climate change. So they’ve decided to concentrate instead on his actions and associates (for instance, the National Rifle Association and neo-Nazis). In the aftermath of the mass shooting in Las Vegas, when Trump offered practically nothing but thoughts and prayers to the victims’ families, The Washington Post ran a Tom Toles cartoon titled “Thoughts and Prayers.” In it, a man labeled nra walks toward the U.S. Capitol carrying a suitcase labeled $ and says: “I don’t think you should consider fundamental gun reform. Please do not.” Where is Trump? Nowhere.

Other cartoonists have chosen to focus on Trump’s many victims—the drowning people of Puerto Rico; the young immigrants being threatened with deportation; and, above all, the wronged, tearful, abused Statue of Liberty. A couple of days after the 2016 presidential election, Lady Liberty was as much a star as the new president. Out of the 20 postelection cartoons displayed by The Daily Telegraph, only 11 included Trump’s body, and many of those also featured the Statue of Liberty—cringing in bed with Trump the morning after, or getting groped and grabbed.

Pat Bagley (Salt Lake Tribune, courtesy of Cagle Cartoons)

NO. 7: HOW DO YOU NOT GO TOO FAR?

One of the most shocking Statue of Liberty cartoons ran before Trump was even nominated as the Republican candidate. On December 9, 2015, the New York Daily News published on its cover Bill Bramhall’s cartoon of Trump holding up the head of Lady Liberty, having just decapitated her. A year and a half later, when the roles were shuffled, the outcome was radically different: When the comedian Kathy Griffin posed holding up a mask of Trump’s bloody head, she was roundly slammed—and not just by Trump supporters. CNN fired her as one of the co-hosts of its New Year’s Eve celebration. Anderson Cooper, her ex-co-host, rebuked her. The image was too close to violent protest, too suggestive of a wish—an effigy more than a piece of humor.

Bill Bramhall (New York Daily News / Getty)

NO. 8: WHO HAS THE GUTS TO BE LIKE CHARLIE HEBDO?

One of the only publications that aims consistently low is Charlie Hebdo, the weekly French satiric magazine. And as we all know, Charlie Hebdo’s equal-opportunity offensiveness has had horrific consequences. On January 7, 2015—just over three years after the magazine ran a drawing on its cover of the Prophet Muhammad threatening “100 lashes, if you don’t die laughing!”—Islamic extremists stormed its offices and murdered 12 people, including the cartoonists known as Wolinski, Cabu, Charb, Honoré, and Tignous.

In the first weeks after the massacre, “Je suis Charlie” was a cry heard around the world. The cartoonists were lionized for their fearlessness in the face of terror. PEN America, the writers’ group, planned to give its Freedom of Expression Courage Award to Charlie Hebdo, in recognition of what PEN’s president, Andrew Solomon, termed the magazine’s vigilance in “patrolling the outer precincts of free speech.” Freedom of expression, even freedom to offend, were the bywords of the day. But these were not the long-term effects of the Charlie Hebdo killings.

NO. 9: DOESN’T GARRY TRUDEAU KNOW BEST?

On April 10, 2015, Garry Trudeau, the creator of Doonesbury, while accepting a Polk Award for lifetime achievement, took the opportunity to attack the morals and judgment of the murdered Charlie Hebdo cartoonists, suggesting that they had brought the trouble onto themselves and also onto the world. How? Trudeau declared that “by attacking a powerless, disenfranchised minority with crude, vulgar drawings closer to graffiti than cartoons, Charlie wandered into the realm of hate speech.”

Shockingly, Trudeau wasn’t alone in his disgust. When PEN announced its plan to give a Courage Award to Charlie Hebdo, six writers who were supposed to host tables at the awards dinner—Peter Carey, Michael Ondaatje, Francine Prose, Teju Cole, Rachel Kushner, and Taiye Selasi—backed out. More than 200 PEN members signed a petition against the accolade. In the end, the award was given, but the upshot of the Charlie massacre seemed to be a warning to cartoonists: Choose the wrong group to offend, and you’re on your own.

NO. 10: IS HATE SPEECH EVER OKAY?

This warning, coming from Trudeau himself—the very cartoonist who has repeatedly yanked Trump’s chain, who declared (in his book Yuge! 30 Years of Doonesbury on Trump) that it would be “comedy malpractice” to ignore such an “asshole,” a figure who “is satire, pure and uncut, free for all to use and enjoy”—was chilling. Suddenly cartoonists were having to check themselves for triggers and hate speech.

But is good political cartooning really possible without hatred? Many of the most effective political cartoons are vicious. They feel like hate because they are hate. They are designed to be inflammatory. In 1832, Honoré Daumier went to jail for lampooning King Louis Philippe as Gargantua excreting favors for the wealthy. Why such harsh punishment for a mere caricature? Jytte Klausen, the author of The Cartoons That Shook the World (about the 2005 publication in Denmark of a dozen Muhammad drawings), has an answer: A drawing can inflame the mind in ways that words simply cannot.

Honoré Daumier

NO. 11: IF YOU INFLAME YOUR READERS, HAVEN’T YOU FAILED?

Some political cartoonists, especially those few with a steady job at a newspaper or magazine, don’t see provocation as part of their job. Quite the opposite. As Kevin Kallaugher (known as KAL), an editorial cartoonist for The Economist and The Baltimore Sun, told The Washington Post, the secret to good political caricaturing is capturing “the subtle things.” If your audience is “too inflamed,” he noted on another occasion, “you’ve failed as a cartoonist.” Your message has been lost.

Back in 2015, shortly after the protest over the PEN America award to Charlie Hebdo, KAL, who had just won the Herblock Award for editorial cartooning, delivered a lecture titled “Where to Draw the Line: Cartooning in the Shadow of Charlie.” He began by pointing out that, unlike in the U.S., “in most places people cannot draw their own head of state. Only 14 percent of the world has the sort of freedom of speech that we do,” and the number is shrinking. As for those rare nations lucky enough to have free speech, KAL added, their citizens have to be careful with that right—or, he seemed to imply, it might get taken away.

NO. 12: HOW DO YOU USE FREE SPEECH WITHOUT LOSING IT?

Free speech is thorny because it is not the same everywhere. You have to know the limits of your audience, your nation, your subject. As KAL said, “Charlie Hebdo is in France for a reason.” After all, France is where, as one comics fan noted, “it’s possible to show Sarkozy mounting a sheep.”

In the U.S. the standards of caricature are different. It’s fine to draw George W. Bush as a monkey, KAL observed. But when it comes to caricaturing Obama this way, well, that’s one of the “places you cannot go.” In 2008 The New Yorkergot in hot water when Barry Blitt, in trying to lampoon people’s fears about the prospect of Barack and Michelle Obama in the White House, portrayed them as terrorists doing a fist bump while the American flag burned in the fireplace.

NO. 13: ISN’T STEREOTYPING ALWAYS BAD?

Regardless of national standards, cartoonists everywhere often rely on stereotypes. And this, as Victor Navasky writes in The Art of Controversy: Political Cartoons and Their Enduring Power, “poses a problem when one is rendering, for example, members of a minority race. How do you make a comment on racism without falling into its trap?” Should Jewish men be drawn with beards and long noses? Isn’t that a racist stereotype? And what about those statues of a fat, castrated Trump with a tiny penis? Don’t they imply that the ultimate weakness is being emasculated—in other words, being a woman?

One of the most memorable caricatures of all time is David Levine’s drawing in The Nation depicting Henry Kissinger in his horn-rimmed glasses, grinning as he screws Mother Earth. It is a perfect portrait of the libidinal force behind Kissinger’s cold political calculations. And it, too, invoked a stereotype of sorts. In 1984, before the caricature ran, 25 staffers at The Nation tried to halt its publication. What enraged them, remembers Navasky, The Nation’s editor at the time, wasn’t the lustful rendering of Kissinger but the fashion in which he screwed the world: “This cartoon reinforced the stereotype that sex was dirty and something that an active male on top does to a passive woman on bottom.” Also, in one woman’s opinion, the female Earth seemed to be enjoying the rape, “gripping the mattress in what could be the grip of passion.”

NO. 14: SINCE EVERYONE IS BOUND TO BE OFFENDED BY SOMETHING, WHAT’S LEFT TO DRAW?

Weighing in on the David Levine flap, Christopher Hitchens, then a Nation columnist, wrote Navasky that he found it “depressing that so many Nation colleagues should confuse the use of a stereotype … with the reinforcement of a stereotype,” adding that “the only safeguard against such a literal mentality would be the adoption of the Islamic code which, in order to be on the safe side, forbids all depictions of the human body as profane.”

The point is, there will always be people who take umbrage at something—and I’m not thinking only of women who object to being represented as happy, passive victims, or those Muslims who believe that any drawing of Muhammad is a crime punishable by death. Some isis members have been so put off by statues of Buddha that they set out to destroy them. Some Jews are offended by swastikas in cartoons or by seeing the name of God written out. Does that mean no one should depict these? Must we listen to everyone who’s offended? Or only to those we agree with? Or only to those in power? Or only to those without power? Or only to those willing to kill for their beliefs?

NO. 15: WHAT IF YOUR EDITOR STOPS YOU?

Many editors are loath to publish any image that could be construed as offensive, because they fear losing readers. This is why, as the cartoonist Daryl Cagle wrote in a piece for the American Society of News Editors, “editors prefer cartoons, drawn in a traditional style, which do not express a strong opinion that some readers might disagree with.” Many cartoonists have absorbed this anxious stance. They censor themselves, making bland cartoons with tired symbols and labels—Uncle Sam, the Republican elephant, the Democratic donkey, the dollar sign. As Cagle noted, “Sometimes a dozen cartoonists will draw the same, obvious gag; we call these matching cartoons ‘Yahtzees.’ ”

This kind of conservatism has led to a two-tier system: While the tamer political cartoons go in family publications, racier ones go out on the websites of (Th)ink, Politico, Truthdig, The Nib, and Cagle, as well as on the websites of newspapers and magazines. There, they compete for attention with gifs and memes. For example, the most-pungent Trump drawings done by Blitt appeared not in The New Yorker’s pages, but on its website. Among the cartoons under the headline “Rejected Trump Sketches by Barry Blitt” was a drawing of Trump snorting one of the white stripes off the American flag as if it were cocaine.

Barry Blitt (Riverhead)

NO. 16: WHAT IF NO EDITOR STOPS YOU?

Generally speaking, the raunchiest caricatures are published not only on the web, but also in alternative comic books and on gallery walls. For instance, last year the artist Judith Bernstein’s exhibit “Cabinet of Horrors,” at the Drawing Center in New York, featured several drawings in which Trump—or, as she terms him, “Frankenschlong”—is rendered, in black slashing strokes, as a dickhead. She uses the same crude imagery for Kim Jong Un and Vladimir Putin. Her angry productions have the energy of bathroom-stall scribblings, which are where she got the idea for them, but they can engender a feeling of nausea and helplessness. What is blind rage without some particular psychological insight into the subject?

NO. 17: SO HOW DO YOU HARNESS FURY?

Consider Warren Craghead, the TrumpTrump author, who draws in a style that’s vaguely reminiscent of the gonzo mode of Ralph Steadman (best known for his work with the journalist Hunter S. Thompson). Craghead, like many cartoonists, does use Trump’s tweets and speech as source material, but he could not possibly be mistaken for a collaborator. He turns Trump’s words against Trump’s person. For instance, in one of his drawings, Trump is shown as a sweaty, fat, hairy man with saggy breasts, and this image is humorously paired with one of Trump’s own insults: “A person who is very flat-chested is very hard to be a 10.”

Warren Craghead III (TRUMPTRUMP / Big Planet Comics)

In another Craghead drawing, the president appears as a wrinkled sea slug with tits, a few hairs coming off the top of his head, and two stubby arms ending in tiny hands. His lower appendage suggests a phallic cloaca rummaging around inside a toy version of the wide-open Capitol building. On the other side of this sea slug is Trump Tower, to which he will presumably carry his booty from the Capitol. A few little Klansmen float in the surrounding slime. In this image of Trump as a greedy, probing slug, Craghead has managed to embody his spectacular selfishness.

NO. 18: CAN ANY ONE BODY PART CAPTURE TRUMP’S TEMPERAMENT?

When Pat Oliphant, David Levine, and Herblock lampooned Nixon, part of what made their cartoons sing was the harmony they drew between his features and his temperament. Nixon’s 5 o’clock shadow was his shadiness, his vulture eyes were his predatory nature, his nose was his intrusiveness. As Doug Marlette, the cartoonist for Newsday, notes, “Nixon looked like his policies. His nose told you he was going to bomb Cambodia.”

But what about Trump? Which body part reveals his essence? His whipped-up hair? His squinty eyes? His small hands making a thumb-and-finger circle? His smirk? Can his specific brand of offense be linked to his specific body, the way Tricky Dick was nailed by Guston?

NO. 19: MUST WE ALL DRAW ASSHOLES NOW?

On January 11, during an Oval Office meeting on immigration reform, Trump gave cartoonists what they’d been looking for. As he spoke his mind about Haiti, El Salvador, and various African nations, the president of the United States reportedly called them “shithole countries,” causing a storm. Suddenly the way was clear. The website for the San Jose Mercury News showed a collection of cartoons in which the shit was allowed to fly. Steve Sack of the Minneapolis Star Tribune showed Trump’s mouth as a toilet full of brown. David Fitzsimmons of the Arizona Daily Star planted Trump’s face right under the tail of the Republican elephant, farting something foul. Bob Englehart, on the website Cagle, drew Trump’s mouth as an asshole spewing the word s***hole.

Steve Sack (Minneapolis Star Tribune, courtesy of Cagle Cartoons)

NO. 20: IS THERE NO OTHER WAY?

Dwayne Booth, known as Mr. Fish, whose work appears in Harper’s and on Truthdig, is the closest we have to an American cartoonist in the Charlie Hebdo mode. He is ruthless to everyone under the sun. But he is not really a caricaturist. Indeed, he tends to avoid making fun of Trump’s body or face, which gives his work an absurdist gravity.

Mr. Fish (And Then the World Blew Up / Fantagraphics)

Mr. Fish’s usual method is to make drawings based on photographs, many of which he pairs with his own outlandish captions and graphic embellishments to represent what Trump might be thinking. That is, he reverses the usual strategy of matching Trump’s caricatured face with his actual words and actions. The cover of Mr. Fish’s new book, And Then the World Blew Up, shows Trump as a suicide bomber, holding a Captain America shield, ready to push the detonator. His expression is one we know well—pouty, narrow-eyed, offended, vengeful. It is a look particular to Trump, his brand of hate, tightly wound up with his very visage.

In another cartoon, which appeared after Hurricane Maria, Mr. Fish offered up a photo-based image of Trump issuing an executive order to change Puerto Rico’s name “to something that sounds a lot less spic-key, because the way it is now makes it hard for me to give a shit, I can tell you.” Yes, the language that Mr. Fish invented for Trump is deeply offensive and racist, fairly dripping with casual hate. But here the hatred is carefully put in its proper place—into the mouth of the 45th president.

This article appears in the April 2018 print edition with the headline “Drawing Donald.”

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